Preparation of “click” binaphthyl stationary phase and its application for separation of anthraquinones from Rheum palmatum L.

Abstract

An organosilane containing binaphthyl functional group was synthesized by clicking 2,2'-bis(prop-2-ynyloxy)-1,1'-binaphthyl with 3-azidopropyltriethoxysilane (AzPTES). The "click" binaphthyl stationary phase was then synthesized by covalently bonding the organosilane onto silica beads. In this synthetic method, the residue of copper iodide (CuI) catalyst can be controlled at a very low level. Polycyclic aromatic hydrocarbons (PAHs) were well retained on the "click" binaphthyl column, and showed different retention factors (k) and separation ratio (α) values from those on octadecylsilyl (ODS) column due to the π-π interaction between the analytes and the stationary phase. The anthraquinone compounds in Rheum palmatum L. were selectively separated and enriched into a fraction by the "click" binaphthyl column. By using this way, the complexity of the sample was largely reduced. Twelve of anthraquinones were recognized by UPLC-ESI-MS/MS. This stationary phase will be very useful for separating and enriching similar compounds with planar aromatic structures from complex traditional Chinese medicine (TCM) samples.

Establishment of a search library about benzylisoquinoline alkaloids based on selective separation on the binaphthyl column and standard analysis on C18 column

“…The columns used in this experiment were the “click” binaphthyl column (150 × 2.1 mm i.d., 5 μm, 10 nm pore size, home made) and XCharge C18 column (150 × 2.1 mm i.d., 5 μm, 10 nm pore size, Sipore Co. Ltd., Dalian, China). All the LC experiment conditions were as follows: Flow rate for the two columns was 0.2 mL/min and column temperature was controlled at 30°C.…”

Evaluation of “click” binaphthyl chiral stationary phases by liquid chromatography

“…3‐Azidopropyltriethoxysilane and (S)‐6,6'‐diphenyl‐1,1'‐bi‐2‐naphthol were prepared according to the reference. CSP1 was synthesized according to a previous article …”

“…The researchers mainly focus on introducing polar substitution groups, such as ―CONH(CH 2 ) n CH 3 , ―CN, ―COOH, and ―CONH 2 , which showed enantioselectivity for some polar carboxamide binaphthyl derivatives. Recently, we reported a “click” binaphthyl column, which showed special retention properties for aromatic compounds through π–π interaction . In this work, the chiral separation ability of the “click” binaphthyl column was evaluated.…”

“…Recently, we reported a "click" binaphthyl column, which showed special retention properties for aromatic compounds through p-p interaction. 25 In this work, the chiral separation ability of the "click" binaphthyl column was evaluated. It showed the ability to separate a wide range of racemic BINOL derivatives including diol, diester, and diether.…”

A Novel Rhein-Functionalized Resin with Application for the Preconcentration of Anthraquinones

“…Recently, a facile solid-phase extraction (SPE) protocol with high selectivity toward flavonoids was established in our previous work using baicalin-functionalized magnetic nanoparticles (Qing et al 2013;Qing et al 2011). Moreover, the ''click'' binaphthyl stationary phase selectively enriched anthraquinones from Rheum palmatum L. by strong p-p interactions (D. Yu et al 2011).…”